Nature is an important souce of various types of antitumor compounds. Recently a novel cytotoxic bistropolone Eupenifeldin was isolated from a culture broth produced by Eupenicillium brefeldianum ATCC 74184. Preliminary testing shows that Eupenifeldin is highly toxic in vitro against HCT-116 and HCT-VM4(human colon carcinoma) cell lines, with IC50 values of 5 ng/ml and 2 ng/ml, respectively. The following proposal describes a highly convergent and enantioselective total synthesis of the title compound. The key steps include the simultaneous introduction of both tropolone units to the eleven-membered core, as well as the stereoselective formation of both dihydropyran rings in a single step. If successful, the proposed route will provide large amount of the natural prouct for further biological evaluation, as well as the possibility to prepare other non-natural analogues for structure-activity relationship studies.